Wayne Douglas Bennett

Wayne Bennett was one of one. The mold from which he was formed was smashed at birth, never to be used again. That was November 3, 1952, when dinosaurs roamed the earth. Or at least the streets of Newton and Framingham, Massachusetts, where he grew up.

Wayne loved his family: His kids, his grandkids, his wife of 25 years, his sister and brothers. He loved his dogs. He loved—and sometimes hated—the Boston Red Sox.

Smoking a turkey, making a roux, cooking a pot of caldo verde: These were his specialties. Salad was always optional. The Southern Comfort was not. Neither were the cigarettes.

He was the smartest person in the room and usually the funniest. He could rub people the wrong way—and often did—but he’d never shine them on. He was generous with his time, his intellect, his middle finger. He’d give you the shirt off his back—unless it was the one that said, “I Was Promised a Handbasket.”

We could mention the fancy schooling that he put himself through, his years as a partner at a Boston law firm, or his time running a software company in Washington, D.C. But we doubt any of that mattered to him nearly as much as the Sox winning the World Series in 2004. And again in 2007. Etcetera.

He was a mathematician, a lawyer, and a fantastic chef. He was a quick thinker and a fast talker. He did the New York Times crossword every day. Wordle, too.

As someone who endured a difficult upbringing, he ensured that his own children did not. As someone who never shied away from hard work, he set an example for everyone around him. As someone who dealt with lawyers and other assorted con artists, he put a premium on the truth.

Wayne died at his home in Helotes, Texas, on September 13, 2026. To say he will be deeply missed is a vast understatement.

He is preceded in death by his brother, David, and his beloved dogs, Trouble and Max.

He is survived by his daughter, Dr. Kyla Bennett (Dr. John Scarborough), his sons, Jason Bennett (Jenny Luna), and Miles Bennett (Ally Melideo), his grandsons Alex and Eli Scarborough, his former wife Terri Tsagaris, his sister Bonnie Benjamin, his brother Scott Bennett, and many other family members and friends across the country.

Family and friends are invited to a celebration of Wayne’s life on Saturday, October 17, at 3pm at Davio’s Back Bay, 75 Arlington St, Boston, MA. In lieu of flowers, please consider a donation to the National Humane Society.